Tetrahydrofuran → 9-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418952ノート

反応式

HRID 418952 の反応式
COC1[CH:4]=[C:5]2[C:14](=[CH:15]C=1)[CH:13](COS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[CH3:37][Mg]Br.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH2:14]([CH:13]1[CH:12]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[C:5]2[C:41]1=[CH:42][CH:43]=[C:44]([O:40][CH3:37])[CH:4]=2)[CH3:15]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl esterHCID 178418573HCID 178418573、化合物

生成物 1

HCID 666519649-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene収率 81%

実験手順

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.151 g, 0.30 mmol), methyl magnesium bromide (0.46 mL, 1.40 mmol), Li2CuCl4 (150 uL), and tetrahydrofuran (3 mL), and stir under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum and flash chromatograph using 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.085 g, 81%) as a white foam. TLC Rf=0.60 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.32 (s, 1H), 7.24 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.42 (m, 1H), 3.23 (s, 1H), 3.08 (dd, 1H, J=12.1, 3.3 Hz), 2.49 (d, 1H, J=13.7 Hz), 1.93 (m, 2H), 1.67 (m, 1H), 1.57 (m, 2H), 1.44 (d, 2H, J=8.8 Hz), 1.19 (m, 3H), 0.62 (t, 3H, J=7.3 Hz).

後処理

  1. concentrationconcentrate
  2. customreaction under vacuum and flash chromatograph

出典と根拠

ORDレコード
ord-aca86e55c0e2414c9b5f8465dc0d507e
出典データセット
uspto-grants-2012_01
特許番号
US08093302B2

反応ノート

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